CA2711555C - Method for conditioning radioactive ion exchange resins - Google Patents
Method for conditioning radioactive ion exchange resins Download PDFInfo
- Publication number
- CA2711555C CA2711555C CA2711555A CA2711555A CA2711555C CA 2711555 C CA2711555 C CA 2711555C CA 2711555 A CA2711555 A CA 2711555A CA 2711555 A CA2711555 A CA 2711555A CA 2711555 C CA2711555 C CA 2711555C
- Authority
- CA
- Canada
- Prior art keywords
- water
- resin
- oxidizing agent
- ion exchange
- exchange resin
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
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Classifications
-
- G—PHYSICS
- G21—NUCLEAR PHYSICS; NUCLEAR ENGINEERING
- G21F—PROTECTION AGAINST X-RADIATION, GAMMA RADIATION, CORPUSCULAR RADIATION OR PARTICLE BOMBARDMENT; TREATING RADIOACTIVELY CONTAMINATED MATERIAL; DECONTAMINATION ARRANGEMENTS THEREFOR
- G21F9/00—Treating radioactively contaminated material; Decontamination arrangements therefor
- G21F9/28—Treating solids
-
- G—PHYSICS
- G21—NUCLEAR PHYSICS; NUCLEAR ENGINEERING
- G21F—PROTECTION AGAINST X-RADIATION, GAMMA RADIATION, CORPUSCULAR RADIATION OR PARTICLE BOMBARDMENT; TREATING RADIOACTIVELY CONTAMINATED MATERIAL; DECONTAMINATION ARRANGEMENTS THEREFOR
- G21F9/00—Treating radioactively contaminated material; Decontamination arrangements therefor
- G21F9/28—Treating solids
- G21F9/30—Processing
- G21F9/301—Processing by fixation in stable solid media
- G21F9/302—Processing by fixation in stable solid media in an inorganic matrix
- G21F9/304—Cement or cement-like matrix
Landscapes
- Physics & Mathematics (AREA)
- Engineering & Computer Science (AREA)
- General Engineering & Computer Science (AREA)
- High Energy & Nuclear Physics (AREA)
- Chemical & Material Sciences (AREA)
- Inorganic Chemistry (AREA)
- Processing Of Solid Wastes (AREA)
- Treatment Of Water By Ion Exchange (AREA)
- Separation, Recovery Or Treatment Of Waste Materials Containing Plastics (AREA)
Abstract
The invention relates to a method for conditioning a contaminated ion exchange resin, by mixing the same with water and at least partly breaking up the same into water--soluble components by means of an oxidising agent added to the water, wherein the resulting aqueous solution is immobilised with a binder, optionally after concentration by evaporation of water.
Description
Description Method for conditioning radioactive ion exchange resins The invention relates to a method for conditioning radioactive ion exchange resins. Ion exchange resins, which are as a rule present as approximately spherical particles, are used, for example in the operation of nuclear facilities, for purifying the coolant of the primary system, i.e. water. The aim of this purification is the avoidance of undesired deposits on the surfaces of the primary circulation components, the avoidance of corrosion and the reduction of the buildup of contamination in the primary circulation of the facility. In this purification, both acidic cation exchangers and basic anion exchangers are used, the former retaining metal cations and the latter retaining anionic compounds, for example metal complexes. Since some of the metals are radionuclides, spent or laden ion exchangers are radioactive waste and must be transported for intermediate or final storage.
Radioactively contaminated exchange resins are also obtained in the decontamination of nuclear facilities, for example in the decontamination of the primary circulation. In such a method, metal oxide layers present on the surfaces of the primary circulation components are detached with the aid of decontamination solutions, the solutions being passed, during or after the decontamination, over ion exchangers in order to remove activity or metal cations present therein.
For the final or intermediate storage, contaminated ion exchangers, which are substantially organic resins having acidic or basic groups, must be conditioned.
Conditioning is to be understood as meaning generally the conversion of radioactive waste into a storable form.
Radioactively contaminated exchange resins are also obtained in the decontamination of nuclear facilities, for example in the decontamination of the primary circulation. In such a method, metal oxide layers present on the surfaces of the primary circulation components are detached with the aid of decontamination solutions, the solutions being passed, during or after the decontamination, over ion exchangers in order to remove activity or metal cations present therein.
For the final or intermediate storage, contaminated ion exchangers, which are substantially organic resins having acidic or basic groups, must be conditioned.
Conditioning is to be understood as meaning generally the conversion of radioactive waste into a storable form.
- 2 -In the case of nuclear facilities, spent ion exchange resins are usually dried and, after a certain storage time or decay time, in which the radioactivity has fallen to a specified limit, are embedded in, for example cemented into, a solid matrix for storage. The embedding of the ion exchange resins in a solid matrix leads to an increase in volume by more than six times the resin volume. Owing to the large amount of resulting waste, the operator of a nuclear power station incurs considerable costs for the intermediate or final storage. Concepts which reduce the volume of the ion exchange resins were therefore developed. One of these concepts envisages incineration. However, this requires complicated filter units in order to prevent emergence of radioactivity into the environment.
Moreover, the incineration does not function particularly well, owing to the acidic or basic groups usually present in the resins. As an alternative, the metals and hence the activity are therefore removed completely from the resins with the aid of acids or alkalis, so that the resins can be reused. The respective acid or alkali is passed over a purely organic resin, i.e. a resin which contains neither acidic nor basic groups and is therefore more easily incineratable, which resin binds the metals (and the activity) by adsorption. During the complete regeneration of the acidic or basic exchange resins, considerable amounts of acid/base are obtained as secondary waste, which has to be disposed of.
A further concept envisages complete mineralization of the exchange resins, leaving only metal salts. In such a procedure, for example disclosed in DE 60 2004 003 464 T2, practically the total resin is oxidized to carbon dioxide and water. This requires very large amounts of oxidizing agents, such as hydrogen peroxide, and an immense outlay in terms of apparatus and process technology, in particular for the 2a purification of the carbon dioxide present as gas.
The invention proposes a method for conditioning contaminated ion exchange resins, with which a volume reduction is associated in comparison with the direct embedding in a solid matrix and which can be carried out in a short time with the use of little material.
CD, 02711555 2014-09-10 This is achieved by mixing the ion exchange resin with water and at least partly breaking up said resin into water-soluble fragments with the aid of an oxidizing agent added to the water, the resulting aqueous solution being consolidated with a binder. The volume reduction achieved by the method compared with cementing in of solid resin particles consists mainly in the transformation from the solid phase, in which the resin is present in the form of a bulky network of macromolecules, into dissolved fragments of this network. The method essentially requires no more than one container for carrying out the resin oxidation and if need be a second container for the consolidation.
The added oxidizing agent causes the polymer network of the resin, for examPle of a copolymer of vinylbenzene and divinylbenzene, to be broken up, water-soluble fragments forming. The water solubility arises from acid or base groups present on the fragments (for example sulfo groups or aminoethyl groups). In order to achieve as large a volume reduction as possible, the oxidation is preferably continued until the total resin or virtually the total resin has gone into solution.
The exchange resin is therefore oxidatively treated only until it is present preferably completely in the form of water-soluble fragments. The resulting amount of carbon dioxide is comparatively small. In addition to carbon dioxide, a small proportion of oxygen, which forms by autoxidation in the case of the use of hydrogen peroxide as an oxidizing agent, may also be present. If the oxidation is continued after the resin is completely present in the form of water-soluble fragments, the advantage according to the invention is achieved to a noticeably smaller extent. According to the invention, an attempt is therefore made to ensure that as large a part as possible of the carbon present in the exchange resin is present in the form of soluble molecular fragments, i.e. is not oxidized to carbon dioxide and water. According to the invention, a degree of oxidation of less than 50%, preferably of less than 20%, of the carbon content of the exchange resin is therefore envisaged. The amount required in each case can be calculated with knowledge of the carbon content of the resin and its chemical structure. Often, corresponding data of the exchange resin are not available so that the required amount of oxidizing agent can then be determined empirically by preliminary experiments. The consolidation is effected in a simple manner by stirring the mixture present at the end of the oxidation treatment with at least the same mass of cement. In addition to cement, other binders, such as waterglass, may optionally also be used. Compared with the direct binding of the untreated ion exchange resin in cement, which is mentioned further above and in which a volume increase by a factor of 6 results in comparison with the original resin bulk volume, a factor of only 2 to 4 is achieved in a procedure according to the invention - depending on the water/resin ratio present and on the water/cement value. This factor can be further reduced if a part of the water is removed by evaporation from the solution prior to consolidation.
Cement, for example Portland cement, generally contains large proportions of calcium oxide, which, in the setting process together with silicates, forms hydrates with the mixing water which bring about the hardening of the cement. If the water of the mixture to be consolidated is acidic, the calcium oxide is dissolved and is no longer available for hydrate formation and hence for the hardening of the cement. In order to prevent this, a base for neutralizing acids or for raising the pH of the mixture is added to the mixture in a preferred variant of the method, so that said mixture is weakly acidic to basic at the end. Alkaline earth metal oxides and hydroxides are preferably used as the base.
The oxidation of the ion exchange resins can be carried out in principle with any desired oxidizing agents.
However, those which, in their reaction with the resin, form no reaction products which hinder the setting of the cement or of another binder are preferably used.
Hydrogen peroxide and ozone are used as oxidizing agents which have this property. Of hydrogen peroxide, only harmless water remains, and ozone is reduced to oxygen, which for the most part escapes from the mixture. In the resin oxidation, 002 (which for the most part escapes) and water form.
The method was tested with various resins. In each case a specified resin volume (50 ml bulk volume, spherical particles, diameter about 1 mm) was mixed with water and 30 percent strength hydrogen peroxide (aqueous solution) was added to this mixture or ozone was passed into said mixture. Further details appear in the following table:
Experi- Water H202 03 Temperature Dissolution ment No. time 1 Resin 1 50 ml 25 ml - - - 80 C 170 min 2 Resin 1 50 ml 25 ml - - - 90 C 40 min
Moreover, the incineration does not function particularly well, owing to the acidic or basic groups usually present in the resins. As an alternative, the metals and hence the activity are therefore removed completely from the resins with the aid of acids or alkalis, so that the resins can be reused. The respective acid or alkali is passed over a purely organic resin, i.e. a resin which contains neither acidic nor basic groups and is therefore more easily incineratable, which resin binds the metals (and the activity) by adsorption. During the complete regeneration of the acidic or basic exchange resins, considerable amounts of acid/base are obtained as secondary waste, which has to be disposed of.
A further concept envisages complete mineralization of the exchange resins, leaving only metal salts. In such a procedure, for example disclosed in DE 60 2004 003 464 T2, practically the total resin is oxidized to carbon dioxide and water. This requires very large amounts of oxidizing agents, such as hydrogen peroxide, and an immense outlay in terms of apparatus and process technology, in particular for the 2a purification of the carbon dioxide present as gas.
The invention proposes a method for conditioning contaminated ion exchange resins, with which a volume reduction is associated in comparison with the direct embedding in a solid matrix and which can be carried out in a short time with the use of little material.
CD, 02711555 2014-09-10 This is achieved by mixing the ion exchange resin with water and at least partly breaking up said resin into water-soluble fragments with the aid of an oxidizing agent added to the water, the resulting aqueous solution being consolidated with a binder. The volume reduction achieved by the method compared with cementing in of solid resin particles consists mainly in the transformation from the solid phase, in which the resin is present in the form of a bulky network of macromolecules, into dissolved fragments of this network. The method essentially requires no more than one container for carrying out the resin oxidation and if need be a second container for the consolidation.
The added oxidizing agent causes the polymer network of the resin, for examPle of a copolymer of vinylbenzene and divinylbenzene, to be broken up, water-soluble fragments forming. The water solubility arises from acid or base groups present on the fragments (for example sulfo groups or aminoethyl groups). In order to achieve as large a volume reduction as possible, the oxidation is preferably continued until the total resin or virtually the total resin has gone into solution.
The exchange resin is therefore oxidatively treated only until it is present preferably completely in the form of water-soluble fragments. The resulting amount of carbon dioxide is comparatively small. In addition to carbon dioxide, a small proportion of oxygen, which forms by autoxidation in the case of the use of hydrogen peroxide as an oxidizing agent, may also be present. If the oxidation is continued after the resin is completely present in the form of water-soluble fragments, the advantage according to the invention is achieved to a noticeably smaller extent. According to the invention, an attempt is therefore made to ensure that as large a part as possible of the carbon present in the exchange resin is present in the form of soluble molecular fragments, i.e. is not oxidized to carbon dioxide and water. According to the invention, a degree of oxidation of less than 50%, preferably of less than 20%, of the carbon content of the exchange resin is therefore envisaged. The amount required in each case can be calculated with knowledge of the carbon content of the resin and its chemical structure. Often, corresponding data of the exchange resin are not available so that the required amount of oxidizing agent can then be determined empirically by preliminary experiments. The consolidation is effected in a simple manner by stirring the mixture present at the end of the oxidation treatment with at least the same mass of cement. In addition to cement, other binders, such as waterglass, may optionally also be used. Compared with the direct binding of the untreated ion exchange resin in cement, which is mentioned further above and in which a volume increase by a factor of 6 results in comparison with the original resin bulk volume, a factor of only 2 to 4 is achieved in a procedure according to the invention - depending on the water/resin ratio present and on the water/cement value. This factor can be further reduced if a part of the water is removed by evaporation from the solution prior to consolidation.
Cement, for example Portland cement, generally contains large proportions of calcium oxide, which, in the setting process together with silicates, forms hydrates with the mixing water which bring about the hardening of the cement. If the water of the mixture to be consolidated is acidic, the calcium oxide is dissolved and is no longer available for hydrate formation and hence for the hardening of the cement. In order to prevent this, a base for neutralizing acids or for raising the pH of the mixture is added to the mixture in a preferred variant of the method, so that said mixture is weakly acidic to basic at the end. Alkaline earth metal oxides and hydroxides are preferably used as the base.
The oxidation of the ion exchange resins can be carried out in principle with any desired oxidizing agents.
However, those which, in their reaction with the resin, form no reaction products which hinder the setting of the cement or of another binder are preferably used.
Hydrogen peroxide and ozone are used as oxidizing agents which have this property. Of hydrogen peroxide, only harmless water remains, and ozone is reduced to oxygen, which for the most part escapes from the mixture. In the resin oxidation, 002 (which for the most part escapes) and water form.
The method was tested with various resins. In each case a specified resin volume (50 ml bulk volume, spherical particles, diameter about 1 mm) was mixed with water and 30 percent strength hydrogen peroxide (aqueous solution) was added to this mixture or ozone was passed into said mixture. Further details appear in the following table:
Experi- Water H202 03 Temperature Dissolution ment No. time 1 Resin 1 50 ml 25 ml - - - 80 C 170 min 2 Resin 1 50 ml 25 ml - - - 90 C 40 min
3 Resin 1 50 ml - - - Passed in in Room 60 hours gaseous form temperature
4 Resin 2 50 ml 25 ml - - - 90 C 2 hours Resin 3 70 ml 40 ml - - - 90 C 6 hours 6 Resin 4 70 ml 35 ml - - - 90 C 5 hours Resins 1 and 2 are a polystyrene-based resin having a relatively low degree of crosslinking and a proportion of about 4 - 6% of divinylbenzene. Resins 3 and 4 are
5 more highly crosslinked and have a proportion of about 8 - 12% of divinylbenzene. The experiments have shown that not all resins are equally degradable. The time required for completely dissolving more highly crosslinked resins (No. 3 and 4) is greater. The temperature is of course also decisive for the duration (cf. experiment No. 1 and 2). Acceleration of the oxidation can also be achieved by adding the hydrogen peroxide in higher concentration. In the case of the oxidation with ozone, the latter was passed in gaseous form into the mixture with the aid of a glass frit.
With ozone, too, complete dissolution of resin 1 was achieved, but a period of 60 hours was required for this purpose. In all cases, the mixture was consolidated with cement at a water-cement mass ratio of 0.5 after complete dissolution of the ion exchange resins. The volume of the resulting hardened cement paste was about twice to three times the resin bulk volume. In all cases, the procedure was effected in alkaline solution.
With ozone, too, complete dissolution of resin 1 was achieved, but a period of 60 hours was required for this purpose. In all cases, the mixture was consolidated with cement at a water-cement mass ratio of 0.5 after complete dissolution of the ion exchange resins. The volume of the resulting hardened cement paste was about twice to three times the resin bulk volume. In all cases, the procedure was effected in alkaline solution.
Claims (10)
1. A method for conditioning a contaminated ion exchange resin, in which the ion exchange resin is mixed with water and at least partly broken up into water-soluble fragments with the aid of an oxidizing agent added to the water, the aqueous solution thus resulting being consolidated with a binder.
2. The method as claimed in claim 1, wherein the aqueous solution is concentrated by evaporation of water before being consolidated with the binder.
3. The method as claimed in claim 1 or 2, wherein the binder is a cement.
4. The method as claimed in claim 3, wherein a base is added to the mixture before consolidation with the cement.
5. The method as claimed in claim 4, wherein the base is an alkaline earth metal oxide or hydroxide.
6. The method as claimed in any one of claims 1 to 5, wherein the oxidizing agent is hydrogen peroxide or ozone.
7. The method as claimed in any one of claims 1 to 6, wherein treatment with the oxidizing agent is carried out at a temperature higher than room temperature.
8. The method as claimed in claim 7, wherein the treatment with the oxidizing agent is carried out at a temperature of from 80°C to 100°C.
9. The method as claimed in any one of claims 1 to 8, wherein the amount of oxidizing agent is chosen so that less than 50% of carbon present in the exchange resin is oxidized to carbon dioxide and water.
10. The method as claimed in any one of claims 1 to 8, wherein the amount of oxidizing agent is chosen so that less than 20% of carbon present in the exchange resin is oxidized to carbon dioxide and water.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102008005336A DE102008005336A1 (en) | 2008-01-17 | 2008-01-17 | Process for conditioning radioactive ion exchange resins |
| DE102008005336.8 | 2008-01-17 | ||
| PCT/EP2009/050415 WO2009090209A1 (en) | 2008-01-17 | 2009-01-15 | Method for conditioning radioactive ion exchange resins |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2711555A1 CA2711555A1 (en) | 2009-07-23 |
| CA2711555C true CA2711555C (en) | 2015-04-14 |
Family
ID=40756569
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2711555A Expired - Fee Related CA2711555C (en) | 2008-01-17 | 2009-01-15 | Method for conditioning radioactive ion exchange resins |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US8372289B2 (en) |
| EP (1) | EP2248134B1 (en) |
| JP (1) | JP5543926B2 (en) |
| KR (1) | KR101183002B1 (en) |
| AT (1) | ATE514168T1 (en) |
| CA (1) | CA2711555C (en) |
| DE (1) | DE102008005336A1 (en) |
| ES (1) | ES2367238T3 (en) |
| TW (1) | TWI442414B (en) |
| WO (1) | WO2009090209A1 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102018131902B3 (en) | 2018-12-12 | 2020-02-27 | Framatome Gmbh | Process for conditioning ion exchange resins and device for carrying out the process |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT43561B (en) | 1909-02-15 | 1910-08-10 | Anton Wrana | Grain grinding and classifying machine. |
| JPS5341319B2 (en) * | 1971-08-17 | 1978-11-01 | ||
| DE2945007A1 (en) * | 1979-11-08 | 1981-05-21 | Kernforschungszentrum Karlsruhe Gmbh, 7500 Karlsruhe | METHOD FOR REPOSITION TIRE, ENVIRONMENTALLY FRIENDLY FASTENING OF RADIOACTIVE ION EXCHANGE RESINS |
| US4437999A (en) | 1981-08-31 | 1984-03-20 | Gram Research & Development Co. | Method of treating contaminated insoluble organic solid material |
| JPS5958400A (en) * | 1982-09-28 | 1984-04-04 | 日本原子力事業株式会社 | Method of volume-decreasing and solidifying radioactive ion exchanging resin |
| JPS5998740A (en) * | 1982-11-30 | 1984-06-07 | Mitsui Eng & Shipbuild Co Ltd | Decomposition treatment of used ion exchange resin |
| US4530723A (en) | 1983-03-07 | 1985-07-23 | Westinghouse Electric Corp. | Encapsulation of ion exchange resins |
| JPH0232600B2 (en) * | 1983-03-07 | 1990-07-20 | Westinghouse Electric Corp | IONKOKANJUSHISUISEIEKIKONGOBUTSUOSEMENTOCHUNIFUNYUSURUHOHO |
| SE8304278L (en) | 1983-08-04 | 1985-02-05 | Studsvik Energiteknik Ab | PROCEDURE FOR TREATMENT OF USE, RADIOACTIVE, ORGANIC ION EXCHANGE MASS |
| JPS61165696A (en) * | 1985-01-18 | 1986-07-26 | 三菱重工業株式会社 | Method of treating radioactive waste |
| JPS63158497A (en) * | 1986-08-20 | 1988-07-01 | 富士電機株式会社 | Decomposing processing method of radioactive ion exchange resin |
| DE3926252A1 (en) | 1989-08-09 | 1991-02-14 | Ghattas Nader Khalil | METHOD AND DEVICE FOR DEGRADING CONSUMED ION EXCHANGE RESINS |
| WO1992003829A1 (en) * | 1990-08-28 | 1992-03-05 | Electric Power Research Institute | Organic material oxidation process utilizing no added catalyst |
| FR2678761B1 (en) * | 1991-07-03 | 1994-07-01 | Commissariat Energie Atomique | BLOCK CONTAINING CONTAMINATED ION EXCHANGE RESINS AND PROCESS FOR PREPARING THE SAME. |
| ES2104956T3 (en) * | 1992-11-04 | 1997-10-16 | Asea Atom Ab | METHOD AND DEVICE FOR THE TREATMENT AND DISPOSAL OF USED ION EXCHANGE RESIN. |
| JP3846820B2 (en) * | 1997-08-20 | 2006-11-15 | 株式会社東芝 | Solid waste treatment method |
| JP4675521B2 (en) * | 2001-08-15 | 2011-04-27 | 日揮株式会社 | Method and apparatus for treating radioactive organic waste |
| JP4414214B2 (en) * | 2003-12-24 | 2010-02-10 | 行政院原子能委員會核能研究所 | Treatment method of waste ion exchange resin |
| ATE346827T1 (en) | 2004-02-13 | 2006-12-15 | Iner Aec | METHOD FOR TREATING USED ION EXCHANGERS |
| EP1786000A1 (en) * | 2005-11-09 | 2007-05-16 | AREVA NP GmbH | Process for treatment of radioactive ion exchange resins |
-
2008
- 2008-01-17 DE DE102008005336A patent/DE102008005336A1/en not_active Withdrawn
-
2009
- 2009-01-15 JP JP2010542625A patent/JP5543926B2/en not_active Expired - Fee Related
- 2009-01-15 WO PCT/EP2009/050415 patent/WO2009090209A1/en active Application Filing
- 2009-01-15 CA CA2711555A patent/CA2711555C/en not_active Expired - Fee Related
- 2009-01-15 AT AT09702004T patent/ATE514168T1/en active
- 2009-01-15 ES ES09702004T patent/ES2367238T3/en active Active
- 2009-01-15 EP EP09702004A patent/EP2248134B1/en active Active
- 2009-01-15 KR KR1020107018247A patent/KR101183002B1/en active IP Right Grant
- 2009-01-16 TW TW098101513A patent/TWI442414B/en not_active IP Right Cessation
-
2010
- 2010-06-16 US US12/816,790 patent/US8372289B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| TWI442414B (en) | 2014-06-21 |
| ATE514168T1 (en) | 2011-07-15 |
| DE102008005336A1 (en) | 2009-07-30 |
| WO2009090209A1 (en) | 2009-07-23 |
| US8372289B2 (en) | 2013-02-12 |
| US20100256435A1 (en) | 2010-10-07 |
| KR20100120155A (en) | 2010-11-12 |
| JP2011510281A (en) | 2011-03-31 |
| KR101183002B1 (en) | 2012-09-18 |
| EP2248134B1 (en) | 2011-06-22 |
| JP5543926B2 (en) | 2014-07-09 |
| ES2367238T3 (en) | 2011-10-31 |
| CA2711555A1 (en) | 2009-07-23 |
| EP2248134A1 (en) | 2010-11-10 |
| TW200941502A (en) | 2009-10-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20130513 |
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| MKLA | Lapsed |
Effective date: 20210831 |
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| MKLA | Lapsed |
Effective date: 20200115 |